1. Superbowl XXXVIII Halftime show a.k.a. ‘Nipplegate’: As Timberlake prepares to take the stage at the race track this weekend, rumors are swirling that he’s been pegged to headline next year’s Super Bowl Halftime Show. There are plenty of reasons why it makes sense for JT to take the gig. For one, 2018 is the 20th anniversary of his old group, N’Sync’s debut release. But chatter about Timberlake at the Super Bowl has reignited conversations about the last time he performed on football’s biggest night.

In 2004, Timberlake was invited by Janet Jackson to appear as a surprise special guest in the finale of her performance. The two performed a duet of “Rock Your Body,” a song by the Neptunes that was originally intended for Jackson’s brother Michael. The song was already considered racy because of its video, which featured JT grinding on a young woman who lip syncs the hook. (It also features a sick beat-boxing section, but that’s beside the point.)

2. What’s in that box? “The weird thing about the digital shorts that I’ve done with Andy [Samberg] and the Lonely Island guys is that we wrote this song in a delirium of no sleep on a Wednesday or Thursday of the week. We recorded it that night, and we were laughing so hysterically — and probably through the delirium of trying to write something so funny, this came out of it,” Timberlake told NPR of his classic 2006 holiday single which went on to win an Emmy for the show.

“We weren’t parodying anyone in particular,” he said. “I think the style in which we were doing the song was early-’90s R&B, so when we had that as a basis, we said, ‘How ridiculous can we make this?'”

3. The “Digital Get Down.” Once upon a time, a little boy band called N’Sync wrote a surprisingly prescient song about the future of sex and relationships. “We’re gettin nasty nasty, we’re getting freaky deaky,” they crooned in the lead in to “Digital Get Down,” before going on to describe an explicit encounter over the phone, that imagines the future of video-based intimacy. Buzzfeed did an excellent breakdown of the song last year. Their TL:DR takeaway? “This song is basically ‘Send nudes’ in 2001.”

4. “Friends with Benefits.” As JT gears up for his F1 appearance, it was just announced that he and co-actress Anna Kendrick will appear in “Trolls Holiday,” a heartwarming sequel to their Dreamworks hit “Trolls,” that will air on NBC on Nov. 24. But back in 2011, JT starred in the much less wholesome flick “Friends with Benefits” (not to be confused with “No Strings Attached” which came out at the same time). “The whole thing was just them banging,” said one of Team 360’s intrepid web producers.

5. ‘Cry Me a River.’ In 2002, in the wake of his golden love story gone wrong with fellow Mouseketeer, Britney Spears, Timberlake released this slow burner of a petty breakup song on his debut solo joint, “Justified.” In the video, jilted JT breaks into his ex-lover’s house so he can have relations with a new lady in her bed. Classy! The video won “Best Male Video” and “Best Pop Video” at the 2003 MTV Video Music Awards.

6. ‘SexyBack.’ You know we couldn’t forget that time in 2006 when our boy JT brought sexy back.